Senior Director of Implementation

About Aiwyn

Aiwyn is the fastest-growing software company serving the accounting profession. Founded in 2020, we now work with 100+ of the largest CPA firms in the world. Our “Job to be done”: speed up cash flow, save Partner time, & deliver best-in-class client experiences. We do this by automating day-to-day firm operations with our Practice Automation solutions. Aiwyn is led by serial entrepreneurs with multiple exits and funded by a Top 10 fintech VC.

About the Role

We’re looking for a Senior Director of Implementation to lead and grow our high-performing implementation team. In this role, you’ll focus on building strategy, strengthening processes, and guiding your team to deliver seamless, high-quality customer onboarding experiences. You’ll set the vision, coach your team to success, and ensure our customers’ transition from sales to “go live” with confidence, clarity, and satisfaction.

You'll collaborate closely with leaders across sales, customer success, support, and product to make sure every client gets the experience they deserve — one that is smooth, timely, and tailored to their needs. As a fast-paced start up, Aiwyn leaders all roll up their sleeves to help get work done. This role will also focus on empowering your team, anticipating capacity needs, and creating the playbooks and strategies that make excellence repeatable.

Key Responsibilities

Team Leadership & Coaching

• Lead, mentor, and inspire a growing implementation team, fostering a customer-first mindset and a culture of collaboration, transparency, and accountability.
• Conduct regular one-on-one meetings and performance check-ins to develop skills, encourage growth, and keep the team engaged and motivated.
• Set clear goals for the team and individuals that align with Aiwyn’s strategic objectives, and track progress toward those goals.

Strategy & Capacity Planning

• Forecast resource needs and balance team capacity to ensure timely delivery across multiple, concurrent implementations.
• Refine and expand our implementation playbook and processes, creating scalable, repeatable methods that improve quality and efficiency.
• Monitor implementation quality using client feedback, internal metrics, and performance data — then turn insights into actionable improvements.

Client Experience & Cross-Functional Collaboration

• Partner with sales to ensure smooth handoffs and create tailored implementation plans that match each client’s needs.
• Work with product, support, and customer success teams to remove roadblocks, resolve escalations, and continuously improve the onboarding journey.
• Promote proactive communication with clients and internal stakeholders to keep projects visible, transparent, and on track.

Team Growth & Onboarding

• Oversee hiring, onboarding, and training for new implementation team members, ensuring they are set up for success from day one.
• Champion the use of our project management tools for visibility, consistency, and best-practice adoption across the team.

Qualifications

About You

• Passionate about building and leading high-performing teams.
• Naturally curious — you dig deeper when something doesn’t work as expected.
• Thrive on solving complex challenges and finding better ways to do things.
• Relentless in your pursuit of excellence for the client, the team, and the business.
• Courageous in voicing ideas, sharing feedback, and driving change.
• Skilled at building trust through empathy, transparency, and follow-through.
• Able to balance ownership of results with openness to feedback and collaboration.

Your Experience

• 7+ years leading implementation teams for SaaS solutions, ideally in an early-stage or growth company.
• Proven track record in strategic leadership — building scalable processes, forecasting capacity, and leading through change.
• Strong project management skills with the ability to oversee multiple implementations at once.
• Excellent communication and problem-solving